Permanent Equity: Investing in Companies that Care What Happens Next

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Ceilings, Scaling & the Death of a Hustler

We see it in founders all the time: If you’re starting a company, you need unparalleled focus, grit, and determination. That dedication is what gets you through the long hours, lack of resources, setbacks, successes, and the work that needs to be done. When you’re starting a company, you hustle and grind because you care, and because it’s the only way to keep the bus moving forward.

But as your company grows (in units, people, scope, or any number of other ways), even if it’s growing linearly, the decisions that need to be made and the work that needs to be done grows exponentially. Continuing to rely on your individual ability will become a ceiling (for your business and for you personally) rather than a springboard. 

It happens in two ways. 

Grinding isn’t scalable.

Okay, it’s not strictly true that grinding isn’t scalable. You can bully a company into growing by personally expanding your effort and hours – but only to a point. We met the owner of an HVAC contractor with a $12M EBITDA who still personally assigned every crew, every morning. It can work, but only if you’re personally super high capacity and never sleep. And it only works as long as you do. 

And, the reality is that small business is a grind. Take this comment from one of our operators: “Why do I keep lulling myself into thinking ‘With all these fires put out today, tomorrow I can finally focus on X & Y?’” Spoiler: Fires spread. Fires start spontaneously. And in business, there will always be another fire. That’s the trap of the grind – and why you’ll always hit a ceiling (even if it’s high) if you haven’t put measures in place to scale. 

Note that in these two examples, “the grind” is also infinite and more or less static. The other nuance to scalability is the difference between grinding out or grinding towards. Gritting through the day-to-day inevitably has limits. Lasting success comes from the grind, but only if that grind comprises a steady compounding of incremental improvements and seemingly insignificant calibrations, and only if those improvements release your capacity to focus on what’s next. 

The grind can feel good. If you’re making the work assignments and putting out fires, you’re needed, and therefore not obsolete. The very qualities that got you where you are will keep you from where you’re going or where you want the business to be. 

Hustlers eventually die.

Hustle has a weird double meaning in our neck of the woods, and the Venn diagram is tenuous. There’s the hustle that stems from the… shadier side of business. These hustles are the ones that flame out when you pry up the floorboards and find a foundation of sand. Yes, these hustlers eventually disappear. And the market is often better for it.

But we also encounter the hustlers that have “hustle.” (Clock the feeling of your high school coach shouting “Good hustle” across the field or court for the difference.) Intimately related to the grind, hustle will get you pretty far. But our bodies, our emotions, our mental health, and our families can only take so much.

In endurance sports like cycling and long-distance running, it’s called a bonk – that moment when you’ve hit a wall and your body stalls out. Will won’t get you moving again, determination doesn’t cut it anymore, and another pot of coffee has no effect.

When you’re out there grinding as a way to scale, the work is also grinding on you, wearing you down and wearing you out. Approaches to work that aren’t sustainable won’t be sustained long term.

Building a sustainable path.

Commitment to growth becomes a forcing function for pushing decisions and work down the organization. In other words, get a little lazier. 

In reality, lazy is an awful lot of work:

Figure out what you’re exceptionally good at, what you like to do, and what no one else can do. And then work to become a teacher of those things, rather than doing them in a vacuum. This means documenting institutional knowledge and processes and giving individual functions true independence while making sure the key to running the business doesn’t just live in your own head.

Hire, mentor, train, and delegate. There’s an uncomfortable tipping point in shifting your efforts from individual grind and reliance on your own hustle to processes and delegation in order to scale. It can feel like you’re becoming obsolete. But the reality is that growth that’s sustainable for you and the company emerges when you become a resource and mentor for competent leaders and team members. 

There are no shortcuts – a willingness to grind and a hustler’s heart are reliable pathways to some level of success. But to turn the corner to sustainability and scale, you’ve also got to release some control.


Pairs well with:

The Kingdom or the Crown: Addressing the Owner Dependence Dilemma in Your Company

Growth Partnerships & the Preservation of Fun